Cycloalkene derivatives and organic electronic devices using the same

Abstract

The present invention relates to a novel cycloalkene derivative, and an organic electronic device using the same. The cycloalkene derivative according to the exemplary embodiment of the present invention may act as a hole injection, a hole transport, an electron injection, an electron transport, or a light emitting material in an organic light emitting diode and an organic electronic device, and in particular, may be used alone as a light emitting host or a dopant.

The invention claimed is: 
     
       1. A compound represented by the following Formula 1, 4-4, or 6-4 or the following compound 5 or 7: 
       
         
           
           
               
               
           
         
       
       
         
           
           
               
               
           
         
       
       
         
           
           
               
               
           
         
         wherein 
         R 1  is disposed at a 2, 9 or 10 position of anthracene and a substituent group represented by —[Ar] m —X, 
         p is an integer of 1 to 3, l is an integer of 1 to 4, and m is an integer of 0 to 5, 
         Ar is a C 6 -C 26  arylene group that is substituted or unsubstituted by C 1 -C 10  alkyl group, a C 6 -C 12  aryl group, a C 2 -C 12  heterocyclic group including N, O or S as a heteroatom, a silyl group or a C 1 -C 10  alkylsilyl group; or a C 2 -C 26  divalent heterocyclic group that is substituted or unsubstituted by a C 1 -C 10  alkyl group, a C 6 -C 12  aryl group, a C 2 -C 12  heterocyclic group including N, O or S as a heteroatom, a silyl group or a C 1 -C 10  alkylsilyl group, and includes N, O or S as the heteroatom, 
         Ar′ is disposed at a 2, 9 or 10 position of anthracene and C 6 -C 26  aryl group that is substituted or unsubstituted by a C 1 -C 10  alkyl group, a C 6 -C 12  aryl group, a C 2 -C 12  heterocyclic group that is substituted or unsubstituted by a C 6 -C 12  aryl group and includes N, O or S as a heteroatom, a silyl group or a C 1 -C 10  alkylsilyl group; or a C 2 -C 26  heterocyclic group that is substituted or unsubstituted by a C 1 -C 10  alkyl group, a C 6 -C 12  aryl group, a C 2 -C 12  heterocyclic group that is substituted or unsubstituted by a C 6 -C 12  aryl group and includes N, O or S as a heteroatom, a silyl group or a C 1 -C 10  alkylsilyl group and includes N, O or S as a heteroatom, 
         X is a substituent group selected from the following Structural Formulas, 
       
       
         
           
           
               
               
           
         
         in the Structural Formulas, Cy is a C 6 -C 26  aryl group or a C 2 -C 26  heterocyclic group including N, O or S as a heteroelement, 
         R 2  is selected from the group consisting of a C 1 -C 10  alkyl group; and a C 6 -C 26  aryl group; 
         n is an integer of 0 to 5, o is an integer of 0 to 10, and in the case where o is 2 or more, R 2 s may be the same as or different from each other, and 
         in the case where l, m or p is 2 or more, Ar, Ar′, or R 1  may be the same as or different from each other. 
       
     
     
       2. The compound according to  claim 1 , wherein the compound that is represented by Formula 1 is selected from the group consisting of the following compounds 4-1 to 4-4, 6-1 to 6-4: 
       
         
           
           
               
               
           
         
       
       
         
           
           
               
               
           
         
         wherein 
         R 1 s are the same as the definitions of Formula 1, and may be the same as or different from each other, 
         Ar's are the same as the definitions of Formula 1, and may be the same as or different from each other. 
       
     
     
       3. The compound according to  claim 1 , wherein the arylene group is selected from the group consisting of a phenylene group, a naphthylene group, a biphenylene group, an anthracenylene group and the following Structural Formulas: 
       
         
           
           
               
               
           
         
       
     
     
       4. The compound according to  claim 1 , wherein m is 0 or 1. 
     
     
       5. The compound according to  claim 1 , wherein R 1  is selected from the group consisting of the substituent groups represented by the following Structural Formulas: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
       6. The compound according to  claim 1 , wherein Ar′ is selected from the group consisting of the substituent groups represented by the following Structural Formulas: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
       7. The compound according to  claim 1 , wherein X is selected from the following Formulas, Cy is C 6  aryl, and n is 1 or more: 
       
         
           
           
               
               
           
         
       
     
     
       8. The compound according to  claim 1 , wherein X is represented by the following Formula, R 1  is disposed at a 9 position of anthracene of Formula 1, and at least one Ar′ is disposed at a 10 position of anthracene: 
       
         
           
           
               
               
           
         
       
     
     
       9. The compound according to  claim 1 , wherein X is represented by the following Formula, p is an integer of 1 to 3, and Ar′ is a substituted or unsubstituted C 6 -C 50  aryl group or a substituted or unsubstituted C 2 -C 50  heterocyclic group including N as a heteroelement: 
       
         
           
           
               
               
           
         
       
     
     
       10. The compound according to  claim 1 , wherein the compound represented by Formula 1 is selected from the group consisting of the following compounds 1 to 4, 8, 11, 13 to 36, 39 to 41, 43 to 69, 72 to 82, 84 to 86: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
       11. An organic electronic device which includes a first electrode, a second electrode, and one or more organic material layers that are disposed between the first electrode and the second electrode, wherein one or more layers of the organic material layers include the compound according to  claim 1 . 
     
     
       12. The organic electronic device according to  claim 11 , wherein the organic material layer includes an electron injection or transport layer, and the electron injection or transport layer includes the above compound. 
     
     
       13. The organic electronic device according to  claim 11 , wherein the organic material layer includes a light emitting layer, and the light emitting layer includes the above compound. 
     
     
       14. The organic electronic device according to  claim 11 , wherein the organic material layer includes a hole injection or transport layer, and the hole injection or transport layer includes the above compound. 
     
     
       15. The organic electronic device according to  claim 11 , wherein the organic electronic device is selected from the group consisting of an organic light emitting diode, an organic phosphorescent device, an organic solar cell, an organic photoconductor (OPC), and an organic transistor. 
     
     
       16. An organic electronic diode which includes a first electrode, a second electrode, and one or more organic material layers that are disposed between the first electrode and the second electrode, wherein one or more layers of the organic material layers include the compound according to  claim 10 .